US6664388B2 - Reagents for oligonucleotide cleavage and deprotection - Google Patents
Reagents for oligonucleotide cleavage and deprotection Download PDFInfo
- Publication number
- US6664388B2 US6664388B2 US10/091,231 US9123102A US6664388B2 US 6664388 B2 US6664388 B2 US 6664388B2 US 9123102 A US9123102 A US 9123102A US 6664388 B2 US6664388 B2 US 6664388B2
- Authority
- US
- United States
- Prior art keywords
- oligonucleotide
- reagent
- deprotection
- solid support
- active methylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 188
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 145
- 238000010511 deprotection reaction Methods 0.000 title claims abstract description 79
- 238000003776 cleavage reaction Methods 0.000 title description 37
- 230000007017 scission Effects 0.000 title description 37
- 238000000034 method Methods 0.000 claims abstract description 105
- -1 methylene compound Chemical class 0.000 claims abstract description 84
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
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- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 claims description 2
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
- C07H21/04—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with deoxyribosyl as saccharide radical
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Abstract
Description
5′ F-CAG TCG CCC TGC C-Q- |
(SEQ ID. NO. 3) |
5′ F-CTT CTT GCT AAT TCC-Q- |
(SEQ ID. NO. 4) |
Claims (61)
Priority Applications (2)
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US10/737,059 US20040191808A1 (en) | 2001-03-08 | 2003-12-16 | Reagents for oligonucleotide cleavage and deprotection |
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US10/737,059 Continuation US20040191808A1 (en) | 2001-03-08 | 2003-12-16 | Reagents for oligonucleotide cleavage and deprotection |
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US10/737,059 Abandoned US20040191808A1 (en) | 2001-03-08 | 2003-12-16 | Reagents for oligonucleotide cleavage and deprotection |
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US (2) | US6664388B2 (en) |
EP (1) | EP1366057B1 (en) |
JP (1) | JP2004521628A (en) |
AT (1) | ATE312841T1 (en) |
CA (1) | CA2468425A1 (en) |
DE (1) | DE60207995T2 (en) |
WO (1) | WO2002072864A2 (en) |
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US20030088088A1 (en) * | 1999-02-04 | 2003-05-08 | Ravikumar Vasulinga T. | Process for the synthesis of oligomeric compounds |
US20030120063A1 (en) * | 1999-05-24 | 2003-06-26 | Invitrogen Corporation | Method for deblocking of labeled oligonucleotides |
US20040044195A1 (en) * | 2002-08-28 | 2004-03-04 | Marek Kwiatkowski | Process for separating and deprotecting oligonucleotides |
WO2008019305A2 (en) * | 2006-08-04 | 2008-02-14 | Ikonisys, Inc. | Improved synthesis of labeled probes |
US20080078535A1 (en) * | 2006-10-03 | 2008-04-03 | General Electric Company | Heat exchanger tube with enhanced heat transfer co-efficient and related method |
US20090221810A1 (en) * | 2004-04-19 | 2009-09-03 | Nanda Dulal Sinha | Process for the removal of exocyclic base protecting groups |
US20110087014A1 (en) * | 2008-04-24 | 2011-04-14 | Girindus America, Inc. | Process for the manufacture of oligonucleotides |
WO2011056872A2 (en) | 2009-11-03 | 2011-05-12 | Gen9, Inc. | Methods and microfluidic devices for the manipulation of droplets in high fidelity polynucleotide assembly |
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US8808986B2 (en) | 2008-08-27 | 2014-08-19 | Gen9, Inc. | Methods and devices for high fidelity polynucleotide synthesis |
US9217144B2 (en) | 2010-01-07 | 2015-12-22 | Gen9, Inc. | Assembly of high fidelity polynucleotides |
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US20040180368A1 (en) * | 2002-12-23 | 2004-09-16 | Affymetrix, Inc. | Method for producing a high density nucleic acid array using activators |
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WO1996032496A2 (en) | 1995-04-03 | 1996-10-17 | Microprobe Corporation | Covalently linked oligonucleotide minor groove binder conjugates |
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DE19627898A1 (en) | 1996-07-11 | 1998-01-15 | Hoechst Ag | Solid phase synthesis of oligonucleotides |
EP0839829A2 (en) | 1996-09-06 | 1998-05-06 | Beckman Instruments, Inc. | Universal solid support oligonucleotide reagents |
US5932718A (en) | 1993-02-01 | 1999-08-03 | Northwestern University | Oligonucleotides having modified internucleoside linkages or terminal amino group |
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WO2000046231A1 (en) | 1999-02-05 | 2000-08-10 | Amersham Pharmacia Biotech Inc. | Method for deprotecting oligonucleotides |
EP1028124A2 (en) | 1999-02-04 | 2000-08-16 | Isis Pharmaceuticals, Inc. | Improved process for the synthesis of oligomeric compounds |
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US5348868A (en) * | 1992-04-24 | 1994-09-20 | Beckman Instruments, Inc. | Methods and reagents for cleaving and deprotecting oligonucleotides |
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- 2002-03-04 JP JP2002571914A patent/JP2004521628A/en active Pending
- 2002-03-04 AT AT02750570T patent/ATE312841T1/en not_active IP Right Cessation
- 2002-03-04 US US10/091,231 patent/US6664388B2/en not_active Expired - Lifetime
- 2002-03-04 EP EP02750570A patent/EP1366057B1/en not_active Expired - Lifetime
- 2002-03-04 CA CA002468425A patent/CA2468425A1/en not_active Abandoned
-
2003
- 2003-12-16 US US10/737,059 patent/US20040191808A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
DE60207995T2 (en) | 2006-08-03 |
US20030181712A1 (en) | 2003-09-25 |
EP1366057A4 (en) | 2004-04-14 |
CA2468425A1 (en) | 2003-09-19 |
EP1366057A2 (en) | 2003-12-03 |
ATE312841T1 (en) | 2005-12-15 |
WO2002072864A3 (en) | 2002-12-27 |
EP1366057B1 (en) | 2005-12-14 |
JP2004521628A (en) | 2004-07-22 |
WO2002072864A2 (en) | 2002-09-19 |
US20040191808A1 (en) | 2004-09-30 |
DE60207995D1 (en) | 2006-01-19 |
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